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HCID 178471922, compound → 3-isobutyryl-8-methoxy-4(1H)-quinolone

HRID 1382280
Notes
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Reaction equation

HRID 1382280 reaction equation
[C:1]([C:6](=[CH:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])[C:7]([O:9]CC)=O)(=[O:5])[CH:2]([CH3:4])[CH3:3]>C1(OC2C=CC=CC=2)C=CC=CC=1>[C:1]([C:6]1[C:7](=[O:9])[C:19]2[C:14](=[C:15]([O:20][CH3:21])[CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)(=[O:5])[CH:2]([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 178471922HCID 178471922, compound

Product 1

HCID 102639013-isobutyryl-8-methoxy-4(1H)-quinoloneYield 52.2%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

Ethyl 2-isobutyryl-3-(2-methoxyphenylamino)acrylate (18.8 g, 0.065 mol) was added in portions to boiling diphenyl ether (150 ml). The mixture was heated under reflux for 30 minutes, cooled, and diluted with petroleum ether (500 ml). Filtration of the mixture gave 3-isobutyryl-8-methoxy-4(1H)-quinolone as a light brown solid (8.32 g, 52.2%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 minutes
  • temperaturecooled
  • filtrationFiltration of the mixture
  • Sources & evidence

    ORD record
    ord-8c9fe1bbb68f47e394415b6a0b4cc2f8
    Source dataset
    uspto-grants-1989_02
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US04806549

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes